This invention relates to novel diazoles, to herbicidal compositions containing them and to the method of using them for controlling the growth of undesired vegetation.
The control of undesired vegetation is desired in many instances. In the most common situation, it is desired to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such useful crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
U.S. Pat. No. 4,127,405, issued to Levitt on Nov. 28, 1978, discloses herbicidal sulfonamides of the formula ##STR1## where R.sub.1 is selected from ##STR2## and where W and Q are independently O or S.
U.S. Pat. No. 4,169,719, issued to Levitt on Oct. 2, 1979, discloses pyrimidine compounds corresponding to the triazines disclosed in the '405 patent.
European Patent Application 81301874.4, published on Nov. 4, 1981, discloses herbicidal pyrrole sulfonamides of the formulas ##STR3## where R.sub.10 is selected from ##STR4##
European Patent Application 80304287.8, published on Jun. 10, 1981, discloses herbicidal compounds of the formulas ##STR5## where W is O or S;
B is ##STR6## R.sub.1 is ##STR7## PA0 Q is ##STR11## R.sub.1 is H, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.4 -C.sub.7 cycloalkylalkyl, (R.sub.17 CH).sub.n C(O)R.sub.16, (R.sub.17 CH).sub.n CO.sub.2 R.sub.18, (R.sub.17 CH).sub.n COSR.sub.19, (R.sub.17 CH).sub.n CONR.sub.20 R.sub.21, (R.sub.17 CH).sub.n SO.sub.2 NR.sub.20 R.sub.21, (R.sub.17 CH).sub.n SO.sub.2 R.sub.22, ##STR12## or C.sub.1 -C.sub.6 alkyl substituted either with (a) 1-3 atoms of F, Br or Cl; or PA0 (1) the total number of carbon atoms in R.sub.1 is less than or equal to 8; and PA0 (2) if R.sub.1 is other than C.sub.1 -C.sub.3 alkyl, then R.sub.3 must be H; PA0 R.sub.2, R.sub.3 and R.sub.4 are independently H or CH.sub.3 ; PA0 R.sub.5 is H, C.sub.1 -C.sub.4 alkyl, --OR.sub.6, NO.sub.2, F, Cl, Br, CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21 ; PA0 R.sub.6 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl C.sub.3 -C.sub.4 alkynyl, CO.sub.2 R.sub.18, SO.sub.2 NR.sub.20 R.sub.21, SO.sub.2 R.sub.22 or C.sub.1 -C.sub.4 alkyl substituted with (a) 1-3 carbon atoms of F, Cl or Br; or (b) OCH.sub.3 ; PA0 (1) when R.sub.5 is other than H, CH.sub.3, OCH.sub.3 or NO.sub.2, then R.sub.6 is H or CH.sub.3 ; and PA0 (2) when R.sub.6 is CO.sub.2 R.sub.18, SO.sub.2 NR.sub.20 R.sub.21 or SO.sub.2 R.sub.22, then R.sub.5 is H, CH.sub.3, OCH.sub.3 or NO.sub.2 ; PA0 R.sub.7 is H or CH.sub.3 ; PA0 R.sub.8 is H, C.sub.1 -C.sub.4 alkyl, --OR.sub.16, NO.sub.2, F, Cl, Br, CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21 ; PA0 R.sub.9 is CH.sub.3 or C.sub.2 H.sub.5 ; PA0 R.sub.10 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, CO.sub.2 R.sub.24, SO.sub.2 NR.sub.20 R.sub.21 or SO.sub.2 R.sub.22 ; PA0 R.sub.11 is H, C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, --OR.sub.16, CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21 ; provided that, when R.sub.10 is other than C.sub.1 -C.sub.3 alkyl, then R.sub.11 is H, Cl, OCH.sub.3, NO.sub.2 or CH.sub.3 ; PA0 R.sub.12 is H or CH.sub.3 ; PA0 R.sub.13 and R.sub.14 are independently H, C.sub.1 -C.sub.3 alkyl --OR.sub.16, F, Cl, Br, NO.sub.2, CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21 ; provided that, when either of R.sub.13 or R.sub.14 is CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21, then the other is H, Cl, CH.sub.3, OCH.sub.3 or NO.sub.2 ; PA0 R.sub.15 is H or CH.sub.3 ; PA0 R.sub.16 is C.sub.1 -C.sub.3 alkyl; PA0 R.sub.17 is H or CH.sub.3 ; PA0 R.sub.18 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA0 R.sub.19 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA0 R.sub.20 and R.sub.21 are independently CH.sub.3 or C.sub.2 H.sub.5 ; PA0 R.sub.22 is C.sub.1 -C.sub.3 alkyl or CF.sub.3 ; PA0 R.sub.23 is H, Cl, Br, CH.sub.3, F, CF.sub.3, OCH.sub.3 or NO.sub.2 ; PA0 R.sub.24 is C.sub.1 -C.sub.3 alkyl or allyl; PA0 R.sub.25 is C.sub.1 -C.sub.3 alkyl; PA0 m is 0, 1 or 2; PA0 n is 0 or 1; PA0 A is ##STR13## X is CH.sub.3, OCH.sub.3, Cl, F, OCF.sub.2 H or SCF.sub.2 H; Y is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2, OCH.sub.2 CF.sub.3, OCF.sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or GCF.sub.2 T where G is O or S and T is H, CHClF, CHBrF, CF.sub.2 H or CHFCF.sub.3 ; PA0 Z is CH or N; PA0 Y.sub.1 is H, Cl, CH.sub.3, OCH.sub.3 or OCF.sub.2 H; PA0 X.sub.2 is OCH.sub.3, CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.2 CH.sub.3, SCH.sub.3 or SCH.sub.2 CH.sub.3 ; PA0 Y.sub.2 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; PA0 X.sub.3 is OCH.sub.3 or CH.sub.3 ; PA0 N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1-(1-methylethyl)-1H-imidazol e-2-sulfonamide, m.p. 185.degree.-186.degree. C.(d); PA0 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1-(1-methylethyl)-1H-im idazole-2-sulfonamide, m.p. 157.degree.-158.degree. C.(d); PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-(1-methylethyl)-1H-imidazo le-2-sulfonamide, m.p. 166.degree.-167.degree. C.; PA0 N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1-ethyl-1H-imidazole-2-sulfon amide, m.p. 196.degree.-197.degree. C.; PA0 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1-ethyl-1H-imidazole-2- sulfonamide, m.p. 178.degree.-179.degree. C.(d); PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-ethyl-1H-imidazole-2-sulfo namide, m.p. 186.degree.-187.degree. C.; and PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-5-bromo-1-methyl-1H-imidazol e-4-sulfonamide, m.p. 205.degree.-206.degree. C. PA0 when R.sub.1 is COR.sub.16, X.sub.a can also be OCOR.sub.16, and PA0 when R.sub.1 is SO.sub.2 R.sub.22, X.sub.a can also be OSO.sub.2 R.sub.22. PA0 R.sub.6 and R.sub.9 are H, CH.sub.3 or CH.sub.2 C.sub.6 H.sub.5 ; PA0 X.sub.a is Cl, Br or I; and PA0 R.sub.9 is CH.sub.3 or CH.sub.3 CH.sub.2.
European Patent Application 81302461.9, published on Dec. 9, 1981, discloses herbicidal thiophenesulfonamides of the formula ##STR8## where R.sub.5 is selected from ##STR9##
Nowhere in the art is there any indication that N-[(heterocyclic)aminocarbonyl]diazole sulfonamides could be prepared or that they would possess herbicidal utility.